CA1157854A - Adenine nucleoside derivatives, their preparation and pharmaceutical compositions containing them - Google Patents

Adenine nucleoside derivatives, their preparation and pharmaceutical compositions containing them

Info

Publication number: CA1157854A
Authority: CA; Canada
Prior art keywords: general formula; cyclaradine; vidarabine; alkoxyalkanoyl; grouping
Prior art date: 1980-06-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000380236A

Other languages

English (en)

French (fr)

Inventor

Robert Vince

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Minnesota System

Original Assignee

University of Minnesota System

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-06-23

Filing date

1981-06-19

Publication date

1983-11-29

1980-06-23 Priority claimed from US06/162,097 external-priority patent/US4362729A/en

1981-01-16 Priority claimed from US06/225,567 external-priority patent/US4338310A/en

1981-06-19 Application filed by University of Minnesota System filed Critical University of Minnesota System

1983-11-29 Application granted granted Critical

1983-11-29 Publication of CA1157854A publication Critical patent/CA1157854A/en

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical class C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 title claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 claims description 32
229960003636 vidarabine Drugs 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
150000005690 diesters Chemical class 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 6
-1 methoxyacetyl group Chemical group 0.000 claims description 5
150000005691 triesters Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 1
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims 1
230000000840 anti-viral effect Effects 0.000 abstract description 9
229940117392 provisc Drugs 0.000 abstract 1
YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
235000013350 formula milk Nutrition 0.000 description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
241000700605 Viruses Species 0.000 description 8
230000003902 lesion Effects 0.000 description 8
229960000643 adenine Drugs 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
229930024421 Adenine Natural products 0.000 description 4
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
229940068196 placebo Drugs 0.000 description 4
239000000902 placebo Substances 0.000 description 4
229940126062 Compound A Drugs 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000006071 cream Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000003871 white petrolatum Substances 0.000 description 3
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
208000007514 Herpes zoster Diseases 0.000 description 2
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000404144 Pieris melete Species 0.000 description 2
101150054830 S100A6 gene Proteins 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
OIRDTQYFTABQOQ-UHFFFAOYSA-N ara-adenosine Natural products Nc1ncnc2n(cnc12)C1OC(CO)C(O)C1O OIRDTQYFTABQOQ-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
210000004392 genitalia Anatomy 0.000 description 2
244000144993 groups of animals Species 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
UGRNVLGKAGREKS-SQEXRHODSA-N (1r,2r,3r,5r)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1C[C@H](CO)[C@@H](O)[C@@H]1O UGRNVLGKAGREKS-SQEXRHODSA-N 0.000 description 1
FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
YOSGSSXHJVWXCX-UHFFFAOYSA-N 7-hexoxyheptanoic acid Chemical compound CCCCCCOCCCCCCC(O)=O YOSGSSXHJVWXCX-UHFFFAOYSA-N 0.000 description 1
102000055025 Adenosine deaminases Human genes 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000448280 Elates Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011543 agarose gel Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
239000006143 cell culture medium Substances 0.000 description 1
229940082500 cetostearyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
206010014599 encephalitis Diseases 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000035876 healing Effects 0.000 description 1
UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
241000701161 unidentified adenovirus Species 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CA000380236A 1980-06-23 1981-06-19 Adenine nucleoside derivatives, their preparation and pharmaceutical compositions containing them Expired CA1157854A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/162,097 US4362729A (en)	1980-06-23	1980-06-23	Alkoxyalkanoate esters of cyclaradine
US162,097		1980-06-23
US225,567		1981-01-16
US06/225,567 US4338310A (en)	1981-01-16	1981-01-16	Alkoxyalkanoate esters of arabinofuranosyladenine

Publications (1)

Publication Number	Publication Date
CA1157854A true CA1157854A (en)	1983-11-29

Family

ID=26858449

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000380236A Expired CA1157854A (en)	1980-06-23	1981-06-19	Adenine nucleoside derivatives, their preparation and pharmaceutical compositions containing them

Country Status (14)

Country	Link
EP (1)	EP0042596B1 (da)
AR (1)	AR230448A1 (da)
AU (1)	AU542271B2 (da)
CA (1)	CA1157854A (da)
DE (1)	DE3162644D1 (da)
DK (1)	DK149026C (da)
ES (1)	ES503221A0 (da)
FI (1)	FI70903C (da)
HU (1)	HU183493B (da)
IE (1)	IE51332B1 (da)
IL (1)	IL63132A (da)
NZ (1)	NZ197458A (da)
PH (1)	PH17109A (da)
PT (1)	PT73237B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4594350A (en) *	1984-07-30	1986-06-10	Reagents Of University Of Minnesota	(3-ethoxypropionate) esters of cyclaradine
EP0219838A3 (en) *	1985-10-22	1988-04-06	Takeda Chemical Industries, Ltd.	Carbocyclic purine nucleosides, their production and use
GB9007569D0 (en) *	1990-04-04	1990-05-30	Nycomed As	Carbo-nucleoside derivatives
WO1991015498A2 (en) *	1990-04-04	1991-10-17	Nycomed Imaging As	Nucleoside derivatives
FR2759091B1 (fr) *	1997-02-06	1999-03-19	Expertises Ind Et	Procede biologique d'obtention de nouveaux derives de l'adenosine et les compositions pharmaceutiques qui les contiennent
CN104297402B (zh) *	2014-07-22	2016-01-20	吉林大学	车前子中腺嘌呤核苷的hplc含量测定方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4055718A (en) *	1976-05-17	1977-10-25	Parke, Davis & Company	9-(2-O-Acyl-β-D-arabinofuranosyl)-adenine compounds and method for their production
US4055717A (en) *	1976-05-17	1977-10-25	Parke, Davis & Company	9-(3-O-Acyl-β-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-β-D-arabinofuranosyl)-adenine compounds, and method for their production
US4069382A (en) *	1976-05-17	1978-01-17	Parke, Davis & Company	9-(5-O-Acyl-β-D-arabinofuranosyl)adenine compounds
US4138562A (en)	1977-02-09	1979-02-06	The Regents Of The University Of Minnesota	Adenosine deaminase resistant antiviral purine nucleosides and method of preparation

1981
- 1981-06-18 AR AR285767A patent/AR230448A1/es active
- 1981-06-18 AU AU71956/81A patent/AU542271B2/en not_active Ceased
- 1981-06-18 DK DK268981A patent/DK149026C/da not_active IP Right Cessation
- 1981-06-18 NZ NZ197458A patent/NZ197458A/xx unknown
- 1981-06-18 FI FI811928A patent/FI70903C/fi not_active IP Right Cessation
- 1981-06-18 IE IE1349/81A patent/IE51332B1/en unknown
- 1981-06-19 DE DE8181104710T patent/DE3162644D1/de not_active Expired
- 1981-06-19 EP EP81104710A patent/EP0042596B1/en not_active Expired
- 1981-06-19 ES ES503221A patent/ES503221A0/es active Granted
- 1981-06-19 PH PH25779A patent/PH17109A/en unknown
- 1981-06-19 CA CA000380236A patent/CA1157854A/en not_active Expired
- 1981-06-19 IL IL63132A patent/IL63132A/xx unknown
- 1981-06-22 HU HU811834A patent/HU183493B/hu unknown
- 1981-06-22 PT PT73237A patent/PT73237B/pt unknown

Also Published As

Publication number	Publication date
IE811349L (en)	1981-12-23
DK149026C (da)	1986-07-07
IE51332B1 (en)	1986-12-10
FI70903B (fi)	1986-07-18
IL63132A0 (en)	1981-09-13
ES8203917A1 (es)	1982-04-01
EP0042596A1 (en)	1981-12-30
PH17109A (en)	1984-06-01
AU7195681A (en)	1982-01-07
PT73237B (en)	1983-04-29
AR230448A1 (es)	1984-04-30
ES503221A0 (es)	1982-04-01
NZ197458A (en)	1983-11-30
FI70903C (fi)	1986-10-27
FI811928L (fi)	1981-12-24
DK268981A (da)	1981-12-24
AU542271B2 (en)	1985-02-14
PT73237A (en)	1981-07-01
HU183493B (en)	1984-05-28
DK149026B (da)	1985-12-23
EP0042596B1 (en)	1984-03-14
IL63132A (en)	1984-06-29
DE3162644D1 (en)	1984-04-19

Legal Events

Date	Code	Title	Description
2000-11-29	MKEX	Expiry

Publication	Publication Date	Title
KR100358327B1 (ko)	2003-03-03	포스포네이트뉴클레오티드에스테르유도체
US6369101B1 (en)	2002-04-09	Therapeutic method to treat herpes virus infection
EP0074306B1 (en)	1988-06-01	Anti-viral guanine derivatives
US4146715A (en)	1979-03-27	2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines
US4287188A (en)	1981-09-01	Purine derivatives
US4816447A (en)	1989-03-28	Anti-viral guanine compounds
CZ283182B6 (cs)	1998-01-14	Guaninové deriváty, způsob jejich výroby a farmaceutické prostředky s jejich obsahem
CS594082A2 (en)	1989-08-14	Method of antiviral effective 2-amino-9-/(2-hydroxy-1-hydroxymethyl-ethoxy)methyl/purines production
EP0915894B1 (en)	2003-05-14	Nucleotide analogs
EP1389970A2 (en)	2004-02-25	Compositions and methods of double-targeting virus infections and cancer cells
KR940010033B1 (ko)	1994-10-21	항비루스 활성을 갖는 화합물의 제조방법
KR840001808B1 (ko)	1984-10-20	아데닌 뉴클레오시드 유도체의 제조방법
EP0042596B1 (en)	1984-03-14	Novel adenine nucleoside derivatives, their preparation and pharmaceutical compositions containing them
US4060616A (en)	1977-11-29	Purine derivatives with repeating unit
US4495180A (en)	1985-01-22	Prodrugs of Ara-A an antiviral agent
Baker et al.	1984	Synthesis and evaluation of a series of 2'-O-acyl derivatives of 9-. beta.-D-arabinofuranosyladenine as antiherpes agents
PT97407B (pt)	1998-08-31	Processo para a preparacao de (r)-9-{2-(fosfono-metoxi)-propil}-guanina
GB2106107A (en)	1983-04-07	(e)-5-(2-bromovinyl)-uridine, its derivatives and a process for the preparation thereof
US4565868A (en)	1986-01-21	Process for preparing guanine derivatives
US20060111327A1 (en)	2006-05-25	Derivatives of triptolide having a high immunosuppressive effect and high water solubility, and uses thereof
EP0226753B1 (en)	1991-04-10	Alpha-tocopherol (halo) uridine phosphoric acid diester, salts thereof, and methods for producing the same
KR0159945B1 (ko)	1999-01-15	신규 시클로부탄 유도체
NO833526L (no)	1984-04-02	Fremgangsmaate for fremstilling av guanidinderivater med anti-virus-virkning
ITRM960851A1 (it)	1998-06-10	Composizioni farmaceutiche per il trattamento di infezioni virali comprendenti una 4 arilcumarina
US5753695A (en)	1998-05-19	Flavilium compounds and method of using